Balapiravir

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319850

CAS#: 690270-29-2

Description: Balapiravir, also known as R1626 and RO4588161, is a polymerase inhibitor and a tri-isobutyl ester prodrug of R1479, was developed to increase bioavailability and improve antiviral activity.


Price and Availability

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Balapiravir, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319850
Name: Balapiravir
CAS#: 690270-29-2
Chemical Formula: C21H30N6O8
Exact Mass: 494.2125
Molecular Weight: 494.505
Elemental Analysis: C, 51.01; H, 6.12; N, 17.00; O, 25.88


Synonym: R1626; R-1626; R 1626; RO4588161; RO-4588161; RO 4588161; Balapiravir.

IUPAC/Chemical Name: (2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-2-azido-2-((isobutyryloxy)methyl)tetrahydrofuran-3,4-diyl bis(2-methylpropanoate)

InChi Key: VKXWOLCNTHXCLF-DXEZIKHYSA-N

InChi Code: InChI=1S/C21H30N6O8/c1-10(2)17(28)32-9-21(25-26-23)15(34-19(30)12(5)6)14(33-18(29)11(3)4)16(35-21)27-8-7-13(22)24-20(27)31/h7-8,10-12,14-16H,9H2,1-6H3,(H2,22,24,31)/t14-,15+,16-,21-/m1/s1

SMILES Code: CC(C(O[C@H]([C@@H]([C@]1(COC(C(C)C)=O)N=[N+]=[N-])OC(C(C)C)=O)[C@@H](O1)N(C=CC(N)=N2)C2=O)=O)C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Feng JY, Xu Y, Barauskas O, Perry JK, Ahmadyar S, Stepan G, Yu H, Babusis D, Park Y, McCutcheon K, Perron M, Schultz BE, Sakowicz R, Ray AS. Role of Mitochondrial RNA Polymerase in the Toxicity of Nucleotide Inhibitors of Hepatitis C Virus. Antimicrob Agents Chemother. 2015 Nov 23;60(2):806-17. doi: 10.1128/AAC.01922-15. PubMed PMID: 26596942.

2: Betson M, Allanson N, Wainwright P. A review of methods to synthesise 4'-substituted nucleosides. Org Biomol Chem. 2014 Dec 14;12(46):9291-306. doi: 10.1039/c4ob01449a. Epub 2014 Oct 10. Review. PubMed PMID: 25302570.

3: Chen YL, Abdul Ghafar N, Karuna R, Fu Y, Lim SP, Schul W, Gu F, Herve M, Yokohama F, Wang G, Cerny D, Fink K, Blasco F, Shi PY. Activation of peripheral blood mononuclear cells by dengue virus infection depotentiates balapiravir. J Virol. 2014 Feb;88(3):1740-7. doi: 10.1128/JVI.02841-13. Epub 2013 Nov 20. PubMed PMID: 24257621; PubMed Central PMCID: PMC3911617.

4: Lim SP, Wang QY, Noble CG, Chen YL, Dong H, Zou B, Yokokawa F, Nilar S, Smith P, Beer D, Lescar J, Shi PY. Ten years of dengue drug discovery: progress and prospects. Antiviral Res. 2013 Nov;100(2):500-19. doi: 10.1016/j.antiviral.2013.09.013. Epub 2013 Sep 27. Review. PubMed PMID: 24076358.

5: Rutter K, Hofer H, Beinhardt S, Dulic M, Gschwantler M, Maieron A, Laferl H, Stättermayer AF, Scherzer TM, Strassl R, Holzmann H, Steindl-Munda P, Ferenci P. Durability of SVR in chronic hepatitis C patients treated with peginterferon-α2a/ribavirin in combination with a direct-acting anti-viral. Aliment Pharmacol Ther. 2013 Jul;38(2):118-23. doi: 10.1111/apt.12350. Epub 2013 May 26. PubMed PMID: 23710895.

6: Nguyen NM, Tran CN, Phung LK, Duong KT, Huynh Hle A, Farrar J, Nguyen QT, Tran HT, Nguyen CV, Merson L, Hoang LT, Hibberd ML, Aw PP, Wilm A, Nagarajan N, Nguyen DT, Pham MP, Nguyen TT, Javanbakht H, Klumpp K, Hammond J, Petric R, Wolbers M, Nguyen CT, Simmons CP. A randomized, double-blind placebo controlled trial of balapiravir, a polymerase inhibitor, in adult dengue patients. J Infect Dis. 2013 May 1;207(9):1442-50. doi: 10.1093/infdis/jis470. Epub 2012 Jul 17. PubMed PMID: 22807519; PubMed Central PMCID: PMC3610419.

7: Nelson DR, Zeuzem S, Andreone P, Ferenci P, Herring R, Jensen DM, Marcellin P, Pockros PJ, Rodríguez-Torres M, Rossaro L, Rustgi VK, Sepe T, Sulkowski M, Thomason IR, Yoshida EM, Chan A, Hill G. Balapiravir plus peginterferon alfa-2a (40KD)/ribavirin in a randomized trial of hepatitis C genotype 1 patients. Ann Hepatol. 2012 Jan-Feb;11(1):15-31. PubMed PMID: 22166557; PubMed Central PMCID: PMC3739984.

8: Li F, Wu X, Hadig X, Huang S, Hong L, Tran T, Brandl M, Alfredson T. Chemical stability of 4'-azidocytidine and its prodrug balapiravir. Drug Dev Ind Pharm. 2010 Apr;36(4):413-20. doi: 10.3109/03639040903225075. PubMed PMID: 19778160.

9: Kronenberger B, Zeuzem S. Future treatment options for HCV: double, triple, what is the optimal combination? Best Pract Res Clin Gastroenterol. 2008;22(6):1123-36. doi: 10.1016/j.bpg.2008.12.002. Review. PubMed PMID: 19187871.

10: Toniutto P, Fabris C, Bitetto D, Fumolo E, Fornasiere E, Pirisi M. R-1626, a specific oral NS5B polymerase inhibitor of hepatitis C virus. IDrugs. 2008 Oct;11(10):738-49. Review. PubMed PMID: 18828074.

11: Pockros P, Nelson D, Godofsky E, Rodriguez-Torres M, Everson GT, Fried MW, Ghalib R, Harrison S, Nyberg L, Shiffman ML, Chan A, Hill G. High relapse rate seen at week 72 for patients treated with R1626 combination therapy. Hepatology. 2008 Oct;48(4):1349-50. doi: 10.1002/hep.22593. PubMed PMID: 18821613.

12: Brandl M, Wu X, Holper M, Hong L, Jia Z, Birudaraj R, Reddy M, Alfredson T, Tran T, Larrabee S, Hadig X, Sarma K, Washington C, Hill G, Smith DB. Physicochemical properties of the nucleoside prodrug R1626 leading to high oral bioavailability. Drug Dev Ind Pharm. 2008 Jul;34(7):683-91. doi: 10.1080/03639040701836636 . PubMed PMID: 18612909.

13: Pockros PJ, Nelson D, Godofsky E, Rodriguez-Torres M, Everson GT, Fried MW, Ghalib R, Harrison S, Nyberg L, Shiffman ML, Najera I, Chan A, Hill G. R1626 plus peginterferon Alfa-2a provides potent suppression of hepatitis C virus RNA and significant antiviral synergy in combination with ribavirin. Hepatology. 2008 Aug;48(2):385-97. doi: 10.1002/hep.22357. PubMed PMID: 18570306.

14: Roberts SK, Cooksley G, Dore GJ, Robson R, Shaw D, Berns H, Hill G, Klumpp K, Najera I, Washington C. Robust antiviral activity of R1626, a novel nucleoside analog: a randomized, placebo-controlled study in patients with chronic hepatitis C. Hepatology. 2008 Aug;48(2):398-406. doi: 10.1002/hep.22321. PubMed PMID: 18553458.